Cheap flights from BOS to HHH (Logan Intl. to Hilton Head Island)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights from BOS to HHH starting at $161 One Way, $328 Round Trip

Prices starting at $328 for return flights and $161 for one-way flights to Hilton Head Island were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Mar 8 - Thu, Mar 12
BOS
Boston
HHH
Hilton Head Island
$328 Roundtrip, found 4 days ago
$328
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Mar 8 from Boston to Hilton Head Island, returning Thu, Mar 12, priced at $328 found 4 days ago
Wed, Apr 22 - Mon, Apr 27
BOS
Boston
HHH
Hilton Head Island
$350 Roundtrip, found 4 days ago
$350
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Apr 22 from Boston to Hilton Head Island, returning Mon, Apr 27, priced at $350 found 4 days ago
Wed, Apr 22 - Mon, Apr 27
BOS
Boston
HHH
Hilton Head Island
$381 Roundtrip, found 4 days ago
$381
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Apr 22 from Boston to Hilton Head Island, returning Mon, Apr 27, priced at $381 found 4 days ago
Sun, Mar 8 - Thu, Mar 12
BOS
Boston
HHH
Hilton Head Island
$383 Roundtrip, found 4 days ago
$383
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Mar 8 from Boston to Hilton Head Island, returning Thu, Mar 12, priced at $383 found 4 days ago
Wed, Apr 22 - Mon, Apr 27
BOS
Boston
HHH
Hilton Head Island
$390 Roundtrip, found 4 days ago
$390
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Apr 22 from Boston to Hilton Head Island, returning Mon, Apr 27, priced at $390 found 4 days ago

Hotel Ideas near Hilton Head Island

Airport Hotels near Hilton Head Island

Hampton Inn Hilton Head

Hampton Inn Hilton Head

2.5 out of 5
1 Dillon Road Hilton Head Island SC
$100 nightly
The price is $110 total per night from Feb 22 to Feb 23
$110 total
Feb 22 - Feb 23
Total with taxes and fees
Book a stay at this golf hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (1,003 reviews)
Everything was wonderful. Our only hesitation for not clicking the top rating was that our toilet wouldn’t flush and we were given another room. There wasn’t someone on duty to help with the issue. Otherwise, all good!

Reviewed on Feb 16, 2026

Hampton Inn Hilton Head
Island Links Resort by Palmera

Island Links Resort by Palmera

3 out of 5
1 Coggins Point Road Hilton Head Island SC
Book a stay at this golf aparthotel in Hilton Head Island. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (328 reviews)
Clean room and responsive customer services. I was not able to use my included 1 hr tennis court reservation because it wasn’t clearly mention that you have to pay equipment rental fee unless you bring your own. I was bit disappointed. It was overall good experience.

Reviewed on Jan 2, 2026

Get rates
Island Links Resort by Palmera
The Westin Hilton Head Island Resort & Spa

The Westin Hilton Head Island Resort & Spa

4 out of 5
2 Grasslawn Ave Hilton Head Island SC
$200 nightly
The price is $220 total per night from Feb 22 to Feb 23
$220 total
Feb 22 - Feb 23
Total with taxes and fees
Book a stay at this beach hotel in Hilton Head Island. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful ...
8.4/10 Very Good! (1,001 reviews)
Room was clean and comfortable, beautiful view. Staff was attentive and the spa was relaxing.

Reviewed on Feb 9, 2026

The Westin Hilton Head Island Resort & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Hilton Head Island

Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive Hilton Head Island SC
$226 nightly
The price is $248 total per night from Feb 26 to Feb 27
$248 total
Feb 26 - Feb 27
Total with taxes and fees
Book a stay at this beach hotel in Hilton Head Island. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the pool and the helpful ...
8.6/10 Excellent! (1,234 reviews)
Excellent stay. Room was spotless and the staff is amazing.

Reviewed on Feb 17, 2026

Sonesta Resort Hilton Head Island
Hilton Beachfront Resort & Spa Hilton Head Island

Hilton Beachfront Resort & Spa Hilton Head Island

4.5 out of 5
1 Hotel Circle Hilton Head Island SC
$190 nightly
The price is $209 total per night from Feb 26 to Feb 27
$209 total
Feb 26 - Feb 27
Total with taxes and fees
Book a stay at this luxury resort in Hilton Head Island. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful ...
8.4/10 Very Good! (1,429 reviews)
Clean. Great staff. Nice views.

Reviewed on Feb 20, 2026

Hilton Beachfront Resort & Spa Hilton Head Island
Coral Sands Resorts by Palmera

Coral Sands Resorts by Palmera

3.5 out of 5
66 Pope Avenue Hilton Head Island SC
Book a stay at this golf aparthotel in Hilton Head Island. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff ...
9.4/10 Exceptional! (869 reviews)
Every door had broken hinges in the room and were very difficult to shut. The pull out bed was broken and would plummet several inches in height randomly when people sat or laid. Most upsetting was the pool. We specifically chose this place and I called in advance to confirm it was heated, they said ...

Reviewed on Dec 27, 2025

Get rates
Coral Sands Resorts by Palmera
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hilton Head Island Hotels With Airport Transportation

Hilton Head Health - Weight Loss Resort and Health Spa

Hilton Head Health - Weight Loss Resort and Health Spa

4 out of 5
14 Valencia Road Hilton Head Island SC
Book a stay at this beach hotel in Hilton Head Island. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Coligny Beach and Coligny Theater ...
Get rates
Hilton Head Health - Weight Loss Resort and Health Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Hilton Head Island Hotels

Red Roof Inn Hilton Head Island

Red Roof Inn Hilton Head Island

2 out of 5
5 Regency Pkwy Hilton Head Island SC
$75 nightly
The price is $83 total per night from Feb 23 to Feb 24
$83 total
Feb 23 - Feb 24
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.4/10 (1,000 reviews)
We had a generally pleasant stay at this property and wouldn't hesitate to stay there again, although the lack of a breakfast was a disappointment (I think the coffee bar photo duped me into thinking they provided it). The only things keeping it from getting 5 stars were how loud we could hear guests ...

Reviewed on Feb 17, 2026

Red Roof Inn Hilton Head Island
Palmera Inn and Suites

Palmera Inn and Suites

3 out of 5
12 Park Ln Hilton Head Island SC
$128 nightly
The price is $141 total per night from Feb 22 to Feb 23
$141 total
Feb 22 - Feb 23
Total with taxes and fees
Stay at this hotel in Hilton Head Island. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,215 reviews)
Clean, location, price

Reviewed on Feb 18, 2026

Palmera Inn and Suites
Hotel Carolina

Hotel Carolina

2 out of 5
9 Marina Side Drive Hilton Head Island SC
$69 nightly
The price is $76 total per night from Feb 22 to Feb 23
$76 total
Feb 22 - Feb 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Hilton Head Island. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and ...
8/10 Very Good! (3 reviews)
The staff were very friendly and helpful. My room had nice new floors and new furniture. The bed was very comfortable. The Roku TV worked well. The bathroom and sink area were clean and very nice. I was pleased that the shower had plenty of hot water. Overall, I enjoyed my stay at the Hotel Carolina! ...

Reviewed on Feb 16, 2026

Hotel Carolina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Hilton Head Island

Omni Hilton Head Oceanfront Resort

Omni Hilton Head Oceanfront Resort

4 out of 5
23 Ocean Lane Hilton Head Island SC
$306 nightly
The price is $332 total per night from Feb 22 to Feb 23
$332 total
Feb 22 - Feb 23
Total with taxes and fees
Book a stay at this beach resort in Hilton Head Island. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the bar in our reviews. ...
9/10 Wonderful! (1,002 reviews)

Families like: Outdoor pools, kids club, kitchenette, playground

Travelers say...
Great location. Resort nice but a bit dated.

Reviewed on Feb 20, 2026

Omni Hilton Head Oceanfront Resort
Sonesta Resort Hilton Head Island

Sonesta Resort Hilton Head Island

4 out of 5
130 Shipyard Drive Hilton Head Island SC
$226 nightly
The price is $248 total per night from Feb 26 to Feb 27
$248 total
Feb 26 - Feb 27
Total with taxes and fees
Book a stay at this beach hotel in Hilton Head Island. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the pool and the helpful ...
8.6/10 Excellent! (1,234 reviews)

Families like: Outdoor pools, kids club, on the beach, bicycle rentals

Travelers say...
Excellent stay. Room was spotless and the staff is amazing.

Reviewed on Feb 17, 2026

Sonesta Resort Hilton Head Island
Hilton Head Island Beach & Tennis Resort

Hilton Head Island Beach & Tennis Resort

3.5 out of 5
40 Folly Field Rd Hilton Head Island SC
Book a stay at this beach hotel in Hilton Head Island. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Popular attractions Coligny Beach and Folly Field ...
7.8/10 Good! (1,000 reviews)

Families like: Outdoor pools, kitchen, playground, on the beach

Travelers say...
Dirty floor and bedding’s

Reviewed on Dec 8, 2025

Get rates
Hilton Head Island Beach & Tennis Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

BOS to HHH Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date

Frequently asked questions

Are there non-stop flights from Logan Intl. Airport to Hilton Head Island Airport (HHH)?
If you're flying from Logan Intl. Airport to Hilton Head Airport, be prepared to change planes. American Airlines, Delta Air Lines and United Airlines are among the airlines that service this route with just one stopover. Use the layover to stretch out your legs and enjoy a coffee!
What is the shortest flight from Logan Intl. Airport to Hilton Head Island Airport (HHH)?
Take the opportunity to kick back and unwind on your way from Boston to Hilton Head Island. The quickest flight time from Logan Intl. Airport to HHH is 3 hours and 45 minutes, which gives you ample time to enjoy a wine or lose yourself in a gripping novel.
How many hours flight from BOS to Hilton Head Airport?
Typically, it takes 3 hours and 51 minutes to jet from BOS to Hilton Head Island Airport (HHH). Get through this medium-haul flight by watching some films and browsing a magazine or two. Alternatively, catch up on some Zs.
What airlines have the most flights from BOS to Hilton Head Airport?
For now, you can't fly nonstop from Logan Intl. Airport (BOS) to Hilton Head Island Airport (HHH). However, you will be able to lock in a flight with one or more stops. There's always a silver lining — use the break to stretch your tired legs or go in search of a nice meal!

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.